NIO

NICOTINIC ACID

Created:	1999-07-08
Last modified:	2024-10-02

Find Related PDB Entry
59 entries where NIO is found as a standalone ligand16 entries where NIO is found in a polymer sequence

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	14
Chiral Atom Count	0
Bond Count	14
Aromatic Bond Count	6

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	NICOTINIC ACID
Systematic Name (OpenEye OEToolkits)	pyridine-3-carboxylic acid
Formula	C₆ H₅ N O₂
Molecular Weight	123.109
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)c1cccnc1
SMILES	CACTVS	3.341	OC(=O)c1cccnc1
SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
Canonical SMILES	CACTVS	3.341	OC(=O)c1cccnc1
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
InChI	InChI	1.03	InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChIKey	InChI	1.03	PVNIIMVLHYAWGP-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00627
Name	Niacin
Groups	nutraceutical approved investigational
Description	Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions.[L7550,L7553,L7556,L7559,L7562,L7565]
Synonyms	Acide nicotinique 3-Pyridinecarboxylic acid 3-Pyridylcarboxylic acid anti-pellagra vitamin ácido nicotínico m-pyridinecarboxylic acid Niacin Niacina β-pyridinecarboxylic acid Nikotinsäure 3-carboxypyridine Nicotinic acid Acidum Nicotinicum pyridine-β-carboxylic acid
Brand Names	Rogenic B-complex Tab Vitamin B Complex Tab Lustime Unicorn healthy mamaBE WELL ROUNDED BE WELL ROUNDED Folika-T Provida DHA Multi-force for Women Tab Nutra Boost Iron, Vit & Min Supp Spectrum 2 Cap B6 Plus Tab Formula Cp Cap Niacin Tablets 500mg USP 50 Plus Nicazyme Multi-phyto Capsules Lip - Fac Formula Cal M Tab TL-Fluorivite Animal Shapes Body Rox Niacin 100 mg Ifb Innersource Tab PROTECT IRON Liquid Vyo Cylate - Pwr Vita-vim With Beta-carotene - Tab Strovite Forte Caplet Tendera-OB Multivitamins and Minerals for Young Women Usana Megavitamin Tablets - Tab Niacin 50mg Vitafol Plus Wellness Formula Simcor Cda-21 Vitamins With Non-medicinal Probiotic Complex Se-Natal Cavan Prenatal Multi-actin OB Complete 400 Red American Eagle Vitamin Supplement Drink Kindervites Mega 13 Multivitamin Formula Niacin 500mg ahoSAN Harvest Of Values All B Complex Tab Niacin-100 Tab 100mg Prenatal Formula Tab Vita Day Tab Abavite Iron Folate Plus WestGel DHA Daily-Vite Novel Vita Lipovitan TriStart DHA Vita-Rx Diabetic Vitamin Vitafol Fe Plus Luna Vitamin and Mineral Bar for Women Nephrocaps-QT Integra TriStart FREE Vitafol OB Caplet Antivert Tab Multi Tabs Escavite D Lipo-B-C Tab Cavan Heme OB Formula Lf Stress Formula Multi-B Comp + 500mg Vit C Cap TriStart ONE Advicor Niacin Tab 100mg USP Vitamin B + C Cap Remedium - Liq Orl Mycelized Childrens Multi-vitamin Liq Orange Flavored Crystal Chews Tab Sveets Card-floe II Tab Multivit with Fluoride Multivitamins and Minerals for Young Men Escavite Lq NovaFerrum Multivitamin with Iron Pediatric Drops Concept OB Niacin Ctr Srt 500mg Reaphirm Plant Source DHA Iron 25mg With Vit B-cmplx, Vit C, Cu & Mo Niacin Cap 250mg Armax Nephrocaps O-Cal Prenatal Vitamin Children's Chewable Tab Master Key Formula 3 Tab Mega Capsules Red Bull Metacinamide Tab Davimet with Fluoride Niaspan Fct Folivane-F Fusion Activator Formula Tab Lipall Plus Tab Cc II Vp-heme Ob DHA Doctor's Choice Brand for Men DermaNIC Multi-Vitamin With Fluoride MVC-Fluoride Irospan 24/6 Niacin-niacinamide Tab NovaMV Multivitamin Formula F L W Protect Plus SO 60 Formula # 7 Tab 50mg Grand Master Formula Tab Hemocyte Plus NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Multitabs One Daily VITES Cool B Lustime Angel Only One - Tablet Men's 50+ Prenatal, DHA Super Stress Mega B Plus 1000mg Vit C Tab Vita Vim With Beta Carotene-caplet C-B Complex Master Key Multi Vitamin Multi Mineral Formula 2 Mhb Multi-Vitamin Fluoride Drops Select OB Sustained Release Niacin 500mg Vita B Complex Tab Lipotropic Ctr Niodan 500 Mg Time Release Tablets Formula Cw Concept DHA Fortistress Tab JEUNCELL Hair restorer and Hair Growth Solution Multicaps Niacin 250mg Niacin Tab 100mg Protect Cardio AF Vitamin B Compound Tab Multi-Vitamin Davimet Formula Cw-caplet Natural Source Spectrum With Beta Carotene Vitafol-OB Plus DHA Prenatal Supplement Plus DHA Multi Vitamin-mineral Formula M-Natal Plus Niacin Tab 100mg Yeast Free Vasodyn Tab Virt-C DHA Vitafol One B3 Folivane-Plus with Ascorbic Acid Precursors Hi Potency B Complex W Chelated Minerals Shen Min Vitamin Supplement Timed Release Vita-vim Srt Vp-pnv-dha One A Day Advance Adults 50+ O-Cal FA multivitamin Niachrom Capsule Adeks Tablets Nata Komplete Poly-Vi-Flor Gummies Niaspan ER Gtf-vitamin-minerals & Pancreatin Tab Vege Swiss One Multivitamin W Chel Mins Tab Vitalife - Capsule Multivitamin with Fluoride Niacin 100mg Tab Multivitamin with fluoride Multi Flow Tablets Gtf Support Caplet Niacin 100 Mg Tablets Poly-Vi-Sol One A Day Advance Adults B-3 500mg Continuous Released Reno Caps Maxum Multi-vite B 6 Plus Niacin 500 Mg and Inositol Pro Hers Vanilla Integra F Iron Folate-F Chromemate Folivane-OB Genicin Vita-S Multi-Vitamin Fluoride and Iron Drops Davimet-M Extra Once A Day Gesticare DHA Niacin 100mg Tablets USP Vitamin B3 Tab 10mg USP Chewable Vitamin B Complex Suppl Provida OB Dr. AVi MULTIVITAMIN with Zinc, Real Ginger, Lemon and Lemongrass Formula Hh Niacin Tab 475mg Niacin Tab 500mg Niacin Tab 50mg Prenatal Mega Antioxidant Men's Complex 5 - Pwr Niacin Tab 250mg Revitalize Multi-vitamin and Mineral Complex Vc II Integra Plus Envirocomplex Nicaprin American Plus Energy & Vitamin Drink Pro Enz Tab Multi Vitamines - Liq Revit Multi-vitamins and Minerals Niacin Tri B3 Src 300mg Acti-niacin Caplet 500mg VITAFOL Gummies Complete One A Day Tab Time Released Niacin 500 mg One-A-day Advance Men's Phytopure American Eagle Energizer Plus Vitamin Supplement Drink Mega Vitaminerals Vita Vim Multivitamins and Minerals Tab Myhephron Dialysis and Stress Supplement Vita Balance 2000 Niacin 100mg PreNatal Vitamins Plus Vita-vim - Tab Multivitamins and Minerals With Betacarotene Tablets bioJET Niacin Caps 100mg Taron-C DHA Vtb Vitamin and Mineral Supplement Lutime Formula O.C. Hsn Formula My Favorite Niacin and Inositol Tab Super Daily No 2 Niacor Phytovim Cap Flush Free Niacin With Inositol Prenatal Ultimate Tab Nitro Vites - Tab Vitafol Caplet Multi #2 Bev 29 Tab Niacin Inj 100mg/ml Vitamin & Mineral Formula 1 Dietary Supplement WesCap-C-DHA Niacin Pwr 800mg/1.25ml Prenatal Vitamins Plus Low Iron Fusion Plus 24 Multivitamins + Minerals Maximum Once A Day Niaspan Puralor Swiss One Timed Release Tab Niacin Src 400mg Dothelle DHA Ni-C-E-LE Plus Hyporyl - Tab
Indication	Niacin is indicated to prevent vitamin deficiencies in pediatric and adult patients receiving parenteral nutrition as part of multivitamin intravenous injections.[L7550,L7553,L7556,L7559] Niacin oral tablets are indicated as a monotherapy or in combination with simvastatin or lovastatin to treat primary hyperlipidemia and mixed dyslipidemia.[L7562,L7565] It can also be used to reduce the risk of nonfatal myocardial infarctions in patients with a history of myocardial infarction and hyperlipidemia.[L7562,L7565] Niacin is also indicated with bile acid binding resins to treat atherosclerosis in patients with coronary artery disease and hyperlipidemia or to treat primary hyperlipidemia.[L7562,L7565] Finally niacin is indicated to treat severe hypertriglyceridemia.[L7562,L7565]
Categories	Agents Causing Muscle Toxicity Cardiovascular Agents Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Diet, Food, and Nutrition Food Growth Substances Hyperglycemia-Associated Agents Hypolipidemic Agents Hypolipidemic Agents Indicated for Hyperlipidemia Lipid Modifying Agents Lipid Modifying Agents, Plain Lipid Regulating Agents Micronutrients Miscellaneous Antilipemic Agents Nicotinic Acid and Derivatives Nicotinic Acids Non-statin Hypolipidemic Agents Indicated for Hyperlipidemia Noxae Organic Anion Transporting Polypeptide 2B1 Inhibitors Peripheral Vasodilators Physiological Phenomena Pyridines Thyroxine-binding globulin inhibitors Toxic Actions Vasodilating Agents Vitamin B Complex Vitamins
ATC-Code	C10AD02 C10AD52 C10BA01 C04AC01
CAS number	59-67-6

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Hydroxycarboxylic acid receptor 3	MNRHHLQDHFLEIDKKNCCVFRDDFIAKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Diacylglycerol O-acyltransferase 2	MKTLIAAYSGVLRGERQAEADRSQRSHGGPALSREGSGRWGTGSSILSAL...	unknown	inhibitor
Hydroxycarboxylic acid receptor 2	MNRHHLQDHFLEIDKKNCCVFRDDFIVKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Nicotinate-nucleotide pyrophosphorylase [carboxylating]	MDAEGLALLLPPVTLAALVDSWLREDCPGLNYAALVSGAGPSQAALWAKS...	unknown	binder
Nicotinamide N-methyltransferase	MESGFTSKDTYLSHFNPRDYLEKYYKFGSRHSAESQILKHLLKNLFKIFC...	unknown	binder
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Thyroxine-binding globulin	MSPFLYLVLLVLGLHATIHCASPEGKVTACHSSQPNATLYKMSSINADFA...	unknown	inhibitor
Organic cation/carnitine transporter 2	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
Monocarboxylate transporter 1	MPPAVGGPVGYTPPDGGWGWAVVIGAFISIGFSYAFPKSITVFFKEIEGI...	unknown	substrate
Sodium-coupled monocarboxylate transporter 1	MDTPRGIGTFVVWDYVVFAGMLVISAAIGIYYAFAGGGQQTSKDFLMGGR...	unknown
Monocarboxylate transporter 4	MGGAVVDEGPTGVKAPDGGWGWAVLFGCFVITGFSYAFPKAVSVFFKELI...	unknown
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682